Reaction of Organolithium Reagents with Lactim Ethers: Preparation of Cyclic 2-Alkyl Imines or 2,2-Dialkyl Amines

Article abstract of DOI:10.1021/jo00197a013

The reaction of lactim ethers 1-3 with organolithium reagents has been found to be an effective method for the preparation of cyclic 2-alkyl imines 4-6.The method is most effective for the preparation of 2-aryl and sterically hindered 2-alkyl imines.In addition, treatment of 1-3 with excess organolithium provides a facile route to the rare cyclic 2,2-dialkyl amine derivatives 7-9.These reactions are characterized by mild reaction conditions and good yields and constitute a superior route to the title compounds.